WiscoREIA upcoming events

WiscoREIA Sheboygan: Boutique Assisted Living: The Quiet Cash Flow Business Hiding in Plain Sight (20 May 2026)

Wed, 20 May 2026 22:30:00 GMT

Boutique Assisted Living: The Quiet Cash Flow Business Hiding in Plain Sight

Join us as Brandon pulls the curtain back on one of the most overlooked and fast growing niches in real estate, boutique assisted living.

He is going to show what this business really looks like, how these homes work, how he finds and buys them, how he finances them, how he sets them up, and how they cash flow like a rental, but with a much bigger long term need behind them.

He is also going to talk about the "silver tsunami" that is happening right now as millions of seniors age into needing care and why small boutique assisted living homes are filling a massive gap that big box facilities are failing at. He will share why this is a real business, how normal people can get involved, and why this asset class is growing into a multi billion dollar space with huge demand over the next several years.

Register now and make sure not to miss this one!

Speaker: Brandon Schwab

Brandon Schwab is a lifelong entrepreneur with 28 years of self-employment experience and a passion for solving broken systems. Since age 15, he’s focused on identifying problems and creating action-driven solutions. His current mission is transforming the senior living industry through Shepherd Premier Senior Living, offering small, home-style communities with significantly higher caregiver-to-resident ratios than traditional facilities.

As Founder and CEO, Brandon is driven to replace family guilt with peace of mind by delivering exceptional care. His goal is to build 300 homes by 2035 to help meet the growing demand for quality senior housing. Known for his energy, clarity, and no-nonsense approach, Brandon continues to raise capital, engage investors, and advocate for better senior care—because doing what’s right can’t wait.

WiscoREIA’s Sheboygan Meeting Always Meets on the 3rd Wednesday of the Month from

5:30 pm to 8:15 pm!

Host: Kyle Kaufman

Kyle Kaufman is a law firm owner, attorney, real estate investor, and host of the Meaningful Ideas Trading Club. Kyle was born and raised in Wisconsin. He grew up wanting to help people. He has discovered his life’s purpose to help families in Wisconsin and to provide individuals with commercial space for their business, and residences for people to live.

In 2005 Kyle started practicing law. He handled almost all aspects of the law. Early in his career he took on landlord and tenant matters, and civil disputes involving real estate. He started to advise people starting their real estate portfolios, and drafted documents for investors to use in their businesses and with tenants and property managers.

In 2010 Kyle became a one-third owner of the law firm, now known as HKK Law Offices (www.hkklawoffices.com). Kyle’s practice shifted to family law sometime around 2018, as more and more people called seeking his assistance. Kyle became fascinated with the financial information he discovered while representing individuals in divorce matters and financial disputes between former significant others. He started to study more thoroughly on the issues of real estate, business, taxes, and more.

Today, Kyle’s law practice focuses entirely on family law, including divorce, maintenance, child support, paternity, property division, child custody, adoption, termination of parental rights, guardianship and more. In the legal world, he sees his contributions in this area to have the most transformational impact on the community. An associate at his law firm practices estate planning.

Kyle now owns one-half of the law firm business and leads a team of 15 people.

Real estate has always been an interest, and after advising clients for many years, Kyle and his wife, Sunny, decided to join in on the fun. In the year 2020, Kyle and Sunny purchased a building with 18 residential units and two commercial units. In 2021, with a partner, they purchased two commercial properties. In 2022, Kyle and Sunny bought a 44,000 square foot warehouse with 3 parking lots. They sold the warehouse in 2025 for a profit. In 2025, they converted their Chicago condo into a rental unit, and then acquired 3 duplexes. They are generating passive income from their investments and using the power of delegation to make it all work.

In 2021 Kyle created an online weekly meetup event called the Meaningful Ideas Trading Club. Kyle hosts the program and invites others to share and mastermind on ideas related to personal and business development.

Outside of business, Kyle and Sunny have 6 children, and they enjoy spending their time with their family.

Make sure to bring tons of business cards as you will be meeting with people that you want to get to know!

Meeting Location:

Legend Larry's

1142 Plankview Green Blvd

Sheboygan Falls, WI 53085

Please enjoy food, drinks, and TIP YOUR SERVERS!

Our Agenda

5:30 PM – Registration Check-In & Networking

• Informal networking with fellow investors

6:00 PM – Meeting Kickoff

• Welcome by Host and/or Co-Host

• WiscoREIA PowerPoint / announcements and updates

• Sponsor Introductions

• Haves & Wants – Share deals, services, and resources

6:30 PM – Deal Case Study

• Breakdown of a real deal with teachable moments (good, bad, ugly)

7:00 PM – Networking Breakouts

• Guest Orientation with Host

• Member & Sponsor general breakout for continued connection

7:15 PM – Main Presentation

• Host introduces Guest Speaker

8:15 PM – Closing Remarks

• Final thoughts and upcoming events

• Invitation to the "Meeting After the Meeting" for more networking

The meeting ends at 8:15 PM, but we’ll continue with an informal after-meeting for anyone who’d like to stay.

You can stay after the meeting as well to network! Remember to bring your deals!

Our doors are open to EVERYONE!

***Make sure to pre-register***

Click here to pre-register!

WiscoREIA Sheboygan: Finding Your Focus as You Build Your Portfolio (17 Jun 2026)

Wed, 17 Jun 2026 22:30:00 GMT

Finding Your Focus as You Build Your Portfolio

Click here to pre-register!

Are you feeling pulled in too many directions with your real estate investing? Not sure what strategy to double down on—or how to scale what you’ve already started?

At this WiscoREIA Sheboygan meeting, we’re diving into what it really takes to find your focus and build a portfolio that actually works for you.

In this session, you’ll learn how to move from scattered efforts to a clear, intentional path—whether you’re just getting started or looking to grow smarter and faster.

In this session, you’ll learn:

✅ Getting started with other people’s money.

Learn how to break into investing without relying solely on your own capital—and how to structure deals that make sense for everyone involved.

✅ Scaling without investors.

Discover strategies to continue growing your portfolio independently and sustainably.

✅ Short-term rentals for lifestyle + tax advantages.

Explore how short-term rentals can add flexibility, increase income, and create unique tax benefits.

✅ Marketing your Airbnb like a pro.

Understand what actually drives bookings—and how to stand out in a crowded market.

✅ Expanding into complementary business lines.

See how adding the right pieces to your business can increase income, reduce risk, and create long-term stability.

Whether your goal is more cash flow, more freedom, or more clarity—this session will help you take the next step with confidence.

Come ready to learn, connect, and walk away with actionable strategies you can start using right away.

Speaker: Margaret Jaberg

Margaret Jaberg currently manages over $2M in investment real estate, with holdings in both long term and short term rentals, as well as related management and hospitality companies. She began creating her own portfolio 7 years ago after a career as a lender and developer for other owner investors. She’ll share stories from the foxholes and suggestions that keep her focused through renovations, tenants and other roadblocks.

WiscoREIA’s Sheboygan Meeting Always Meets on the 3rd Wednesday of the Month from

5:30 pm to 8:15 pm!

Host: Kyle Kaufman

Kyle now owns one-half of the law firm business and leads a team of 15 people.

Outside of business, Kyle and Sunny have 6 children, and they enjoy spending their time with their family.

Make sure to bring tons of business cards as you will be meeting with people that you want to get to know!

Meeting Location:

Legend Larry's

1142 Plankview Green Blvd

Sheboygan Falls, WI 53085

Please enjoy food, drinks, and TIP YOUR SERVERS!

Our Agenda

5:30 PM – Registration Check-In & Networking

• Informal networking with fellow investors

6:00 PM – Meeting Kickoff

• Welcome by Host and/or Co-Host

• WiscoREIA PowerPoint / announcements and updates

• Sponsor Introductions

• Haves & Wants – Share deals, services, and resources

6:30 PM – Deal Case Study

• Breakdown of a real deal with teachable moments (good, bad, ugly)

7:00 PM – Networking Breakouts

• Guest Orientation with Host

• Member & Sponsor general breakout for continued connection

7:15 PM – Main Presentation

• Host introduces Guest Speaker

8:15 PM – Closing Remarks

• Final thoughts and upcoming events

• Invitation to the "Meeting After the Meeting" for more networking

The meeting ends at 8:15 PM, but we’ll continue with an informal after-meeting for anyone who’d like to stay.

You can stay after the meeting as well to network! Remember to bring your deals!

Our doors are open to EVERYONE!

***Make sure to pre-register***

Click here to pre-register!